Pyrrolidine → 4-(Pyrrolidin-1-YL)but-2-YN-1-OL

HRID 454107Notes

Reaction equation

HRID 454107 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:7][C:8]#[C:9][CH2:10][OH:11]>C1(C)C=CC=CC=1>[N:1]1([CH2:7][C:8]#[C:9][CH2:10][OH:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 2027752-Butyn-1-ol, 4-chloro-

Product 1

HCID 142786094-(Pyrrolidin-1-YL)but-2-YN-1-OLYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Pyrrolidine (7.8 ml, 94 mmol) was added dropwise to a solution of 4-chlorobut-2-yn-1-ol (4.74 g, 45 mmol) in toluene (40 ml) and the mixture stirred and heated at 60° C. for 1 hour. The volatiles were removed by evaporation and the residue was purified by chromatography eluting with methylene chloride/methanol (96/4) to give 4-(pyrrolidin-1-yl)but-2-yn-1-ol (4.3 g, 69%).

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue was purified by chromatography
  3. washeluting with methylene chloride/methanol (96/4)

Sources & evidence

ORD record
ord-926f1cb6ba804c30bb020b060fd02fe6
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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